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| Date | Match | Score |
|---|---|---|
| 07.09.2025 | Dunbeholden - Montego Bay United | 1 : 2 |
| 06.04.2025 | Montego Bay United - Dunbeholden | 4 : 0 |
| 02.02.2025 | Dunbeholden - Montego Bay United | 2 : 0 |
| 10.11.2024 | Montego Bay United - Dunbeholden | 2 : 1 |
| 20.03.2024 | Dunbeholden - Montego Bay United | 0 : 2 |
| 17.12.2023 | Montego Bay United - Dunbeholden | 1 : 2 |
| 09.04.2023 | Dunbeholden - Montego Bay United | 4 : 0 |
| 08.01.2023 | Montego Bay United - Dunbeholden | 0 : 2 |
| 10.04.2022 | Montego Bay United - Dunbeholden | 0 : 1 |
| 24.01.2022 | Dunbeholden - Montego Bay United | 3 : 0 |
| Date | Match | Score | Res |
|---|---|---|---|
| 24.05.2026 | Mount Pleasant Academy - Montego Bay United | 2 - 3 | W |
| 21.05.2026 | Montego Bay United - Cavalier | 0 - 2 | L |
| 17.05.2026 | Cavalier - Montego Bay United | 0 - 1 | W |
| 06.05.2026 | Mount Pleasant Academy - Montego Bay United | 2 - 1 | L |
| 03.05.2026 | Montego Bay United - Treasure Beach | 0 - 2 | L |
| Date | Match | Score | Res |
|---|---|---|---|
| 06.05.2026 | Waterhouse - Dunbeholden | 4 - 0 | L |
| 03.05.2026 | Dunbeholden - Mount Pleasant Academy | 0 - 5 | L |
| 26.04.2026 | Treasure Beach - Dunbeholden | 1 - 0 | L |
| 23.04.2026 | Dunbeholden - Harbour View | 4 - 0 | W |
| 19.04.2026 | Dunbeholden - Tivoli Gardens | 2 - 0 | W |